DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This application, filed 29 October, 2024, is a national stage application of PCT/KR2023/005788, filed 27 April, 2023, which claims foreign benefit of application KR10-2022-0053491, filed 29 April, 2022.
Information Disclosure Statement
Two information disclosure statements (IDS) submitted on 29 October, 2024 and 28 May, 2026 are acknowledged and have been considered.
Status of the Application
Receipt is acknowledged of Applicant's claimed invention, filed 29 October, 2024, in the matter of Application N° 18/861,273. Said documents have been entered on the record.
Claims 12-13 and 15 are amended. Claims 14 and 17-20 are canceled. Claims 21-24 are new. No new matter was introduced.
Thus, Claims 1-13, 15-16 and 21-24 represent all claims currently under consideration.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1 and 3-7 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites “a compound comprising a 5-pentylfurfural (5-PF) structure of the following Formula 2.” The transitional term “comprising” is open-ended and does not exclude additional, unrecited elements. See MPEP §2111.03. Accordingly, the claim is not limited to the compound depicted in Formula 2, but encompasses compounds comprising the recited Formula 2 structure together with additional, unspecified structural matter. However, the claim does not define what additional structural matter may be present, where such additional matter may be attached to the recited 5-PF structure, or otherwise provide boundaries by which one of ordinary skill in the art could determine the scope of compounds encompassed by the claim. Accordingly, the metes and bounds of the claimed “compound comprising” the Formula 2 structure are unclear.
Claims 3-7 are dependent from Claim 1, and fail to cure the deficiencies as stated above.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 12 and 21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Morash et al. (WO 2021/050927 A2).
Morash teaches an anti-fungal composition comprising a yeast-exuded fungicide which is 5-pentyl-2-furaldehyde, also known as 5-pentylfurfural and instant Formula 2 (‘927, Para 0009-0010, Claim 9).
The characterization or intended use of the composition does not distinguish the claimed composition from the composition expressly disclosed by Morash where the compositions are otherwise the same (comprising 5-PF as an active ingredient.) See MPEP §2112.01; "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Accordingly, to the extent the preamble or other language characterizes the composition according to an intended use or purpose, such language does not impart a structural distinction over the composition expressly disclosed by the reference.
As such, Morash anticipates Claims 12 and 21.
Claims 12 and 21 are rejected under 35 U.S.. 102(a)(1) as being anticipated by Koitabashi et al. (JPH 10218718 A, published 1998).
Koitabashi teaches an antimicrobial composition which contains 5-pentyl-2-furaldehyde, also known as 5-pentylfurfural and instant Formula 2, as an active ingredient (‘718, Abstract).
The characterization or intended use of the composition does not distinguish the claimed composition from the composition expressly disclosed by Koitabashi where the compositions are otherwise the same (comprising 5-PF as an active ingredient.) See MPEP §2112.01; "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Accordingly, to the extent the preamble or other language characterizes the composition according to an intended use or purpose, such language does not impart a structural distinction over the composition expressly disclosed by the reference.
As such, Koitabashi anticipates Claims 12 and 21.
Allowable Subject Matter
Claims 8-11, 15-16 and 23-24 are allowed.
Claim 1 would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action.
Claims 3-7 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
Claims 2, 13 and 22 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The closest prior art of record includes Moussallem et al. (Tetrahedron, Vol. 68, pp.8617-8621, 2012, cited in IDS and ISR), Stensrud (WO 2014/179156 A1 English version of KR10-2016-0003771A, cited in IDS and ISR), and Kirchhecker et al. (Green Chem., 2015, 17, 4151–4156).
Moussallem teaches the preparation of substituted furfural intermediates, to include 5-pentylfurfural (5-PF), using butyllitium (BuLi) and dimethylformamide (DMF) in diethyl ether (EtO2) during a multistep synthesis directed to benzodifuran-furan conjugated materials. However, the reference employs the formylation reaction merely as an intermediate synthetic step and neither discloses nor suggests the specifically recited process steps for preparing 5-pentylfurfural (5-PF), including the sequence of adding BuLi dissolved in hexane to the Formula 1 compound dissolved in an aprotic organic solvent, followed by addition of DMF to the resulting reaction product, as recited in the independent process claims. Furthermore, Moussallem does not provide a teaching or suggestion that would have motivated a person skilled in the art to modify the intermediate synthetic step to arrive at the specifically claimed preparation method. Additionally, Moussallem neither teaches nor suggests amino acid derivatives of 5-PF, pharmaceutical compositions or dietary supplement compositions comprising such derivatives, or methods of treating disease using such derivatives.
Stensrud likewise teaches preparation of 5-PF by alkylation of a 5-(hydroxymethyl)furfural (HMF)-sulfonate precursor, specifically by reacting HMF-triflate with a pentyl Grignard reagent in THF (‘156, Pg. 10, Table 2). Although Stensrud therefore teaches the preparation of 5-PF itself, Stensrud does not disclose or suggest the presently claimed method, but rather employs a different starting material and synthetic pathway involving sulfonation of HMF followed by Grignard alkylation. Stensrud further discloses amino-acid-containing HMF derivatives, including an HMF-derived aldehyde reacted with glycine to form a Schiff base followed by reduction; however, Stensrud does not disclose or suggest an amino-acid derivative of 5-PF. Thus, although Stensrud separately teaches preparation of 5-PF and preparation of certain amino-acid-containing HMF derivatives, the reference provides no teaching or suggestion to combine these distinct disclosures so as to arrive at the presently claimed 5-PF-amino acid compounds, nor a reason for one of ordinary skill in the art to do so with a reasonable expectation of success.
Additionally, Stensrud neither teaches nor suggests, pharmaceutical compositions or dietary supplement compositions comprising such derivatives, or methods of treating disease using such derivatives.
Kirchhecker teaches amino acid derivatives of unsubstituted furfural compounds prepared through condensation of furfural with amino acids. However, Kirchhecker neither discloses nor suggests the use of 5-PF as the aldehyde substrate, nor the presently claimed 5-PF-amino acid derivatives.
Therefore, although the prior art independently teaches preparation of 5-pentylfurfural and, separately, amino acid derivation of other furan aldehydes, the prior art neither teaches nor reasonably suggests modifying 5-PF in the presently claimed manner to produce the compounds of Formulae 3 and 4, nor would it have provided one of ordinary skill in the art with a reason to do so with a reasonable expectation of success.
Moreover, Examiner searches did not identify any reference disclosing the presently claimed 5-PF-AA derivatives or their therapeutic use at the time the invention was made. Accordingly, the prior art of record, whether considered alone or in combination, does not teach or suggest Claims 1-11, 15-16 and 23-24, which are therefore considered to be novel and nonobvious over the prior art of record.
Communication
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Donna M. Nestor whose telephone number is (703)756-5316. The examiner can normally be reached generally (w/flex): 5:30a-5p EST M-Th.
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/D.M.N./ Examiner, Art Unit 1627
/Kortney L. Klinkel/ Supervisory Patent Examiner, Art Unit 1627
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